Sodium hydride → 2-[(1-Methyl-4-piperidinyl)oxy]-5-nitropyridine

HRID 2273081노트

반응식

HRID 2273081 반응식
[H-].[Na+].Cl[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][N:5]=1.[OH:13][CH:14]1[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]1>C1COCC1>[CH3:20][N:17]1[CH2:18][CH2:19][CH:14]([O:13][C:4]2[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][N:5]=2)[CH2:15][CH2:16]1

참가 물질

5

반응물 3

HCID 24758Sodium hydride2회HCID 660484-Piperidinol, 1-methyl-HCID 783082-Chloro-5-nitropyridine

생성물 1

HCID 529048992-[(1-Methyl-4-piperidinyl)oxy]-5-nitropyridine수율 49.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

557 mg of NaH (14 mmol) suspended in 10 ml of THF are placed under nitrogen. The mixture is cooled to 0° C. and a solution of 1.5 g (9.3 mmol) of 2-chloro-5-nitropyridine and 1.28 g (11.1 mmol) of 4-hydroxy-1-methylpiperidine in 15 ml of THF is added dropwise. The reaction mixture is refluxed for 4 hours. After hydrolysing the excess NaH, the solvent is evaporated off under reduced pressure. The residue is taken up in ethyl acetate and washed with water and then with saturated NaCl solution. It is then dried over Na2SO4 and filtered, and the filtrate is evaporated under reduced pressure. The residue is chromatographed on silica gel, eluting with a DCM/MeOH mixture from (100/0 v/v) up to 100/4 v/v) to give 1.1 g of 2-(1-methylpiperidin-4-yloxy)-5-nitropyridine.

후처리

  1. temperatureThe reaction mixture is refluxed for 4 hours
  2. customthe solvent is evaporated off under reduced pressure
  3. washwashed with water
  4. dry with materialIt is then dried over Na2SO4
  5. filtrationfiltered
  6. customthe filtrate is evaporated under reduced pressure
  7. customThe residue is chromatographed on silica gel
  8. washeluting with a DCM/MeOH mixture from (100/0 v/v) up to 100/4 v/v)

출처 및 근거

ORD 기록
ord-4d9e1ae15a884949b0e7493e37eef7ff
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09120812B2

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